Acetic Acid → HCID 88103065, compound

HRID 411113Notes

Reaction equation

HRID 411113 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[C:10]([CH:14]=[S:15](=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:18]([CH3:21])([O-:20])=[O:19].C(O)(=O)C.C([O-])(=O)C.[NH4+]>O>[Cl:1][C:2]1[C:11]([CH:12]=[CH:21][N+:18]([O-:20])=[O:19])=[C:10]([CH:14]=[S:15](=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 18539788HCID 18539788, compound

Product 1

HCID 88103065HCID 88103065, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With the exclusion of atmospheric moisture, 50 g (0.18 mol) of methyl 2-chloro-3-formyl-4-sulfonylmethylbenzoate, 220 g (3.6 mol) of nitromethane, 216 g (3.6 mol) acetic acid and 7 g (91 mmol) of ammonium acetate are stirred at 85° C. The reaction mixture is poured into 2 l of distilled water and extracted with diethyl ether. The organic phase is washed with saturated aqueous sodium bicarbonate solution, dried with sodium sulfate, filtered and freed from the solvent under reduced pressure. The crude product is recrystallized from n-hexane/ethyl acetate. Yield: 13.1 g, m.p. 147-150° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase is washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customThe crude product is recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-6f5869fd3b1147cd93691d6be80afc61
Source dataset
uspto-grants-2003_05
Patent number
US06559100B1

Reaction notes

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